endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate

Base Information

• Chemical Name: endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate
• CAS No.: 167640-43-9
• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.444

Synonyms:endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate

Chemical Property of endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate

Chemical Property:

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Technology Process of endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate

There total 2 articles about endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

methanol (67-56-1) + di<(1'R,2'S,5'R)-menthyl> (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate (167640-42-8) → dimethyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate (167819-43-4) + endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate (167640-43-9)

Guidance literature:

With methanesulfonic acid; for 156h; Heating;

DOI:10.1002/hlca.19940770802

Reference yield:

di<(1'R,2'S,5'R)-menthyl> (2R,3R)-7-oxabicyclo<2.2.1>hept-5-ene-2-endo,3-exo-dicarboxylate (167640-41-7) → endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate (167640-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / diethyl ether / 0 - 20 °C

2: 38 percent / MeSO₃H / 156 h / Heating

With methanesulfonic acid; hydrogen; palladium on activated charcoal; In diethyl ether;

DOI:10.1002/hlca.19940770802

Reference yield: 32.0%

endo-<(1'R,2'S,5'R)-menthyl> exo-methyl (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate (167640-43-9) → (1'R,2'S,5'R)-menthyl (2R,3R)-3-exo-(hydroxymethyl)-7-oxabicyclo<2.2.1>heptane-2-endo-carboxylate

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -50 - 20 ℃;

DOI:10.1002/hlca.19940770802

upstream raw materials:

methanol

di<(1'R,2'S,5'R)-menthyl> (2R,3R)-7-oxabicyclo<2.2.1>heptane-2-endo,3-exo-dicarboxylate

di<(1'R,2'S,5'R)-menthyl> (2R,3R)-7-oxabicyclo<2.2.1>hept-5-ene-2-endo,3-exo-dicarboxylate

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